The Sunset Celebration: Behind the Scenes

In the Florida Keys we are all about the sun. Almost every day is sunny. Visitors from all over the world come to enjoy it – most appreciative as of late are our cold northern friends! The Keys are one of the rare locations where a person can easily enjoy both sunrises and sunsets over the water simply by walking across the road. With all of the magnificent beauty the sun provides it’s no wonder we’ve made a tradition of celebrating the sunset every night. Up and down the Overseas Highway you will find people pulling their cars off the road to take a picture, sitting along the water’s edge or out on a deck somewhere taking in the vibrant orange, red and yellow hues.

Dianne6The nightly Sunset Celebration in Key West is the mac daddy of all the sunset reverence going on in the Keys. Every night, beginning two hours before the sun goes down, you can go down to Mallory Square and join a couple thousand other people to celebrate the setting of the sun. You’ll find an amazing variety of street performers, food carts, psychics, artists and even a few pretty odd dudes to entertain you.

For those of us who live in the Keys, Mallory Square is the one event we always end up taking our visitors to see so we’re all pretty familiar with characters like the Cat Man but have you ever wondered how this relatively large event manages to go on successfully night after night? or how it even got started in the first place?

Dianne4Mallory Square has a long history as a gathering place. It was first a favorite anchorage for pirates, then a base for anti-pirating in the 1800’s. It was the center of the wrecking industry in Key West and a place to assemble soldiers in four wars.

In more recent history, Mallory became a gathering place for hippies in the 1960’s to watch the sunset high on LSD and it grew from there. By the late 70’s people were setting up areas to sell their wares on the dock in spite of the City’s best efforts to stop them. Brick and mortar shops nearby started to complain, and with renovations going on to accommodate the cruise ships, the area was starting to get a little crazy.  This is when a small group of vendors and entertainers realized that the tradition that had been created was in dire need of some organization if they expected it to survive.

The Key West Cultural Preservation Society Inc. was established in 1984. They met with the City of Key West, negotiated a lease, set up some ground rules that both parties could live with and the Sunset Celebration ( became an official entity.

Dianne2A couple of hours before the sun goes down, vendors, artists and performers who have been juried into the fold gather towards the back of Mallory Square to draw numbers to determine who gets to set up where. The members with more seniority get top pick of the best spots.

The KWCPS leases the area for four hours a night and are required to provide the security, clean-up and insurance for the event. This is no small feat when you consider the fact that a couple thousand people are in attendance most nights. They have to run a tight ship.

Antonio, an acrylic artist who sets up his display at least five nights a week allowed me to sit with him one evening and learn about his career as a Mallory Square artist. This event is his main gig. It is the way that he has supported his family and is now using to send his daughter to school. The Sunset Celebration has provided him a livelihood that has allowed him to focus on what he loves best, painting. Antonio was born in Cuba and came to the US during the Mariel Boat Lift on a shrimp boat with his family in the early 1970’s. This month marks the 35th anniversary of that mass exodus of Cubans to America. 125,000 were said to have come to the US during that event. It’s amazing the rich history and fascinating stories that you can find when you share a sunset with someone.

Dianne5Almost every night of the year, unless it gets rained out, you can come see the Sunset Celebration at Mallory Square, enjoy the creative, lively atmosphere and see an unbelievably beautiful sunset.

When you do, make sure to take a few minutes to talk with the people of Mallory Square to learn about their unique way of life. You’ll be glad you did.

As editor of Island Jane and FishMonster Magazines it is my job to bring you the very best of the Florida Keys. I am an avid diver, I love to kayak and paddleboard and I even like to fish a little bit 🙂 I love living in the Florida Keys and I hope I can share some of that with you.